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Process for preparing thioesters from oxothioglycolic acid compounds

A technology for thioglycolic acid and compounds, which is applied in the field of palladium-catalyzed preparation of thioesters by oxothioglycolic acid compounds, can solve problems such as complicated operations, and achieve the effects of simple operations, simplified processing methods, and optimized synthesis strategies.

Active Publication Date: 2021-08-13
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This scheme often requires the participation of heating and higher pressure carbon monoxide, but the industrial operation of the high temperature, high pressure and highly toxic system is more complicated

Method used

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  • Process for preparing thioesters from oxothioglycolic acid compounds
  • Process for preparing thioesters from oxothioglycolic acid compounds
  • Process for preparing thioesters from oxothioglycolic acid compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Embodiment 1, preparation S-(p-tolyl) 4-acetophenone thioester

[0066]

[0067] Following general procedure A, the yields are shown in Table 1.

[0068] Utilize nuclear magnetic resonance to analyze the S-(p-tolyl) 4-acetophenone thioester obtained in embodiment 1, obtain result:

[0069] 1 H NMR (400MHz, CDCl 3 )δ8.07(dd, J=20.9,8.5Hz,4H),7.40(d,J=8.1Hz,2H),7.28(d,J=7.9Hz,2H),2.66(s,3H),2.41( s,3H). See figure 1 .

[0070] 13 C NMR (101MHz, CDCl 3)δ 197.3, 190.2, 140.6, 140.2, 140.0, 134.9, 130.3, 128.6, 127.7, 123.2, 26.9, 21.4. See figure 2 .

Embodiment 2

[0071] Embodiment 2, preparation S-(p-tolyl) 4-formylbenzenethio ester

[0072]

[0073] Following general procedure A, the yields are shown in Table 1.

[0074] Utilize nuclear magnetic resonance to analyze the S-(p-tolyl) 4-formylphenyl thioester obtained in embodiment 2, obtain result:

[0075] 1 H NMR (400MHz, CDCl 3 )δ10.10(s,1H),8.16(d,J=8.0Hz,2H),7.99(d,J=8.1Hz,2H),7.39(d,J=7.9Hz,2H),7.34–7.21( m,2H),2.41(s,3H).

[0076] 13 C NMR (101MHz, CDCl 3 )δ191.4, 190.1, 141.1, 140.3, 139.5, 134.9, 130.3, 129.9, 128.0, 123.1, 21.4.

Embodiment 3

[0077] Embodiment 3, preparation S-(p-tolyl) 4-fluorophenylthio ester

[0078]

[0079] Following general procedure A, the yields are shown in Table 1.

[0080] Utilize nuclear magnetic resonance to analyze the S-(p-tolyl) 4-fluorophenylthio ester obtained in embodiment 3, obtain the result:

[0081] 1 H NMR (400MHz, CDCl 3 )δ8.10–8.00(m,2H),7.42–7.35(m,2H),7.27(d,J=7.9Hz,2H),7.21–7.10(m,2H),2.41(s,3H).

[0082] 13 C NMR (101MHz, CDCl 3 )δ189.2, 166.05(d, J=255.3Hz), 140.0, 135.1, 133.03(d, J=3.1Hz), 130.2, 130.06(d, J=9.3Hz), 123.5, 115.90(d, J=22.1Hz) ,21.4.

[0083] 19 F NMR (376MHz, CDCl 3 )δ-105.2.

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Abstract

The present invention provides a method for preparing thioesters from oxothioglycolic acid. In the presence of a palladium catalyst, a phosphine ligand and an organic solvent, the corresponding thioester is generated by decarboxylation of an oxythioglycolic acid compound and reaction with an aryl iodide / aryl bromide or a compound containing an unsaturated bond. The method provided by the invention can realize high-efficiency catalytic conversion at room temperature or under heating, the reaction conditions are mild, the operation is simple, no additional additives such as alkali are used, the treatment method is simplified, and it meets the requirements of developing green and environment-friendly chemistry. The scope of substrates And functional group compatibility has universal applicability and high chemoselectivity. And this method can be successfully applied to the scheme of functional group modification of complex molecules to optimize the synthesis strategy of some drug molecules, improve the synthesis efficiency and reduce the cost, which has industrial synthesis value and prospect.

Description

technical field [0001] The invention relates to the field of compound synthesis, in particular to a palladium-catalyzed method for preparing thioesters through oxothioglycolic acid compounds. Background technique [0002] Thioester is a very important class of synthetic intermediates in organic chemistry. Through further functionalization reactions, sulfur atoms and carbonyl groups can be easily introduced into various structures, which will greatly change the physical and chemical properties of the compound and can be applied to Activation modification of various bioactive molecules and other fields. In addition, the high reactivity of sulfur atoms and carbonyl groups is also widely used in the field of synthesis, which makes thioesters an organic molecule with high synthetic value. [0003] At present, the main scheme for the construction of thioesters is the carbonyl intercalation system of thiol-carbon monoxide: under the catalysis of transition metals, thiol, carbon mo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C327/26C07D307/68C07F5/02C07F7/08C07D307/42C07D213/80C07D213/803C07J31/00C07D333/70C07C327/22C07C327/24C07D295/185C07D209/86C07K5/065
CPCC07B2200/07C07C327/22C07C327/24C07C327/26C07D209/86C07D213/80C07D213/803C07D295/185C07D307/42C07D307/68C07D333/70C07F5/025C07F7/081C07F7/083C07J31/003C07K5/06078C07C2601/14
Inventor 傅尧赵斌尚睿刘德光王光祖
Owner UNIV OF SCI & TECH OF CHINA
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